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Abstract
A stereoselective total synthesis of each of the two diastereomeric C6-hydroxyethyl analogs of (−)-9-nor-9β-hydroxyhexahydrocannabinol has been reported. Control of the stereochemistry at C6 during the key step is accomplished through an intramolecular oxymercuration reaction. The prediction that the analogs would exhibit different degrees of binding to the cannabinoid receptor was borne out. This observation sheds light on the stereochemical requirements of the receptor.
Published Version
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